Dyestuffs of the naphthoylene-arylimidazol-peri-dicarboxylic acid series



ETA

United States Patent DYESTUFFS OF THE NAPHTHOYLENE-ARYL- IMIDAZOL-PERI-DICARBOXYLIC ACID SERIES Wilhelm Eckert and Otto Fuchs, Frankfurt am Main, and

Wilhelm Happe, Schwalbach (Taunus), Germany, assignors to Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Briining, Frankfurt am Main, Germany, a corporation of Germany No Drawing. Filed Feb. 11, 1958, Ser. No. 714,471

Claims priority, application Germany Feb. 16, 1957 6 Claims. (Cl. 260-282) The present invention relates to valuable new dye stuffs of the naphthoylene-arylimidazol-peri-dicarboxylic acid series and to a process of preparing the same; more particularly it relates'to dyestufis corresponding to the following general formula wherein R stands for a substituted or unsubstituted arylene radical and R; has the meaning indicated above. The dyestuffs can be used for dyeing fibers or foils of polyesters, especially of polyethylene glycol terephthalates, from an aqueous suspension and possess on these materials very good properties of fastness.

Now we have found that the affinity of these dyestuffs for polyester fibers can be considerably increased, when the radical R of the amine is substituted by an alkoxy group. The process can be carried out by condensing naphthoylene-arylimidazol-peri-dicarboxylic acids or their anhydrides in an organic solvent or in water with compounds of the type X-NH in which X stands for a 2,965,644 Patented Dec. 20, 1960 CHzOHrCHa-O-Ri wherein R means a substituted or unsubstituted arylene radical and R represents a low-membered branched or straight-chained alkyl group.

The new dyestuffs dye fibers or foils of polyesters considerably deeper tints than the dyestuffs disclosed in German Patent No. 547,924. The dyeings can be produced from an aqueous suspension at about 100 C. in,

the presence of a carrier, such as o-phenylphenol or tetrahydronaphthalene, or at temperatures above 100 C. under pressure without the addition of a carrier.

Before the dyeing operation the dyestutfs are advantageously finely dispersed according to known methods by grinding them with a dispersing agent in a roller or oscillating mill or according to another method.

The following examples serve to illustrate the invention, but they are not intended to limit it thereto, the parts being by weight unless otherwise stated and the relationship of parts by weight to parts by volume bein the same as that of the kilogram to the liter.

Example 1 of polyesters, especially of polyethylene glycol tereph thalates, vivid golden-yellow tints of excellent properties of fastness.

It corresponds to the following formula- 3 Example 2 300 parts of naphthoylene-4'-cyano-benzimidazol-peridi carboxylic anhydride and 90 parts of 3-ethoxy-propylamine are heated at the boil for 2 hours in 2500 parts by volume of pyridine. On cooling the dyestuff separates in the form of fine yellow little crystals. It is filtered ofi with suction, washed with methanol and dried. In a finely dispersed form the dyestuff dyes fibers of polyesters brilliant greenish yellow tints of very good properties of fastness.

The pyridine used as solvent can be replaced by other inert solvents, such as picoline. quinoline. o-dichlorobenzene, trichlorobenzene or a-chloronaphthalene.

Example 3 354 parts of naphthoylene-4.-methyl-benzimidazol-peridicarboxylic anhydride and 120 parts of 3-isopropoxypropylamine are heated under reflux for some hours in 5000 parts by volume of water. After cooling the reaction product is filtered ofi? with suction, washed well with water and dried. The dystuff so obtained dyes polyester fibers vivid golden-orange tints of very good properties of fastness.

' The following table indicates a number of further dyestulfs which can be obtained by the process of this invention and also the tints of the dyeings produced with these dyestuffs on polyester fibers, which likewise possess good properties of fastness:

TABLE nap'hthoylene-aryllmidazol-pcricondensed tint dicarboxylic acid or its anhydride with 1, naphthoylene b nzimidazol peri di- 3-methoxygoldencarboztylio acid or its anhydridc. propylayellow mine.

2. naphthoylene- 4 chloro benzlmida- 3-ethoxy-pro- Do.

zollgieri-dicarboxylic acid or its anhypylamine.

3. naphthoylene -4 chloro benzimida- 3-isopropoxy- D0.

zoI-peri-dicarboxyiic acid or its anhypropyledride. mine.

4. naphthoylene-4 cyano-benzimidazol- 3-rnethnxygreenish peri-dicarboxyhc acid or its anhypropylayellow. dride. mine.

5. naphthoylcne-i' cyano-benzimidarol- 3-n-butoxy- Do.

peri-dicarboxylic acid or its anhypropyledride. mine.

6. naphthoylene 4 methyl-benzirr'ida- Zimethoxygoldenzolrperiwdicarboxylic acid or its anhypropylaorange dride. Irina.

7. naphthoylene 4' methyl -benzimida- 3-cthoxy- Do.

zol-perl-dicarboxylic acid or its anhypropyla drlde. mine.

8. naphthoylene 4 -methyl-benzirrlda- 3-n-butoxy- Do.

zol-peri-dicarboxylic acid or its anhypropyledride. mine.

9. naphthoyleno-4-methox v benzimlda- 3-methoxyred-brown.

zol-peri-dicarboxylie acid or its anhypropyladride. mine.

to. na-phthoylenei -isopropoxy-bonzlmido D0.

dazol-peri-dicarboxylic acid or its anhydride.

11'. naphthoylene-t-lsopropoxy-benzimi- 3-isopropoxy- Do.

dazol-peri-dlcarboxylic acid or its anpropylehydridc. mine.

12. naphthoylene-4'-lsopropoxy-benzimi- 3-n-butoxy- Do.

dazol-pcri-dlcarboxylic acid or its anpropylahydride. mine.

We claim:

1. Dyestuffs which correspond to the following general formula CHzCHzCHz-O-R wherein R represents a member selected from the group consisting of phenylene, chloro-phenylene, cyano-phenylene, methyl-phenylene, methoxy-phenylene and propoxyphenylene, and R represents a lower alkyl group.

2. The dyestufi which corresponds to the following formula I l N 1 3. The dyestuff which corresponds to the following formula (lJH2-0HiCH20OHa N 4. The dyestufi which corresponds to the following formula ([lHzCHr-CH;OCH;

N 0:6 to

5 6 5. The dyestuff which corresponds to the following 6. The dyestuff which corresponds to the following formula formula cm-cm-om-ocm filHr-CHa-CHrOCEI; l 6 1 o=e o=o l l l References Cited in the file of this patent UNITED STATES PATENTS 1,935,945 Eckert Nov. 21, 1933 FOREIGN PATENTS 301,173 Italy Sept. 28, 1932 

1. DYESTUFFS WHICH CORRESPOND TO THE FOLLOWING GENERAL FORMULA 